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Water → HCID 11182227、化合物

HRID 1826243
ノート
印刷プレビュー

反応式

HRID 1826243 の反応式
Br[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=1.Cl[P:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C(OCC)C>[C:23]1([P:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:2]2[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 66180ChlorodiphenylphosphineHCID 9921361N-(6-Bromopyridin-2-yl)-2,2-dimethylpropanamide

生成物 1

HCID 11182227HCID 11182227、化合物収率 27%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

1.00 g (3.89 mmol) of 6-bromo-2-pivaloylaminopyridine from example 14.2.1 was dissolved in 10 ml of diethyl ether and admixed at 0° C. with 3.64 ml (8.00 mmol) of (iso-C3H7)MgBr (2.2M in Et2O). The suspension was stirred at 0° C. for 18 h and then admixed with 0.7 ml (0.86 g, 3.89 mmol) of chlorodiphenylphosphine. The mixture was allowed to warm to ambient temperature overnight and was then hydrolyzed by adding 10 ml of dist. H2O. The resulting phases were separated and the aqueous phase was extracted twice with 50 ml each time of ethyl acetate. The organic phases were combined and dried over Na2SO4, and the solvent was removed under reduced pressure. The residue was filtered together with dichloromethane through a short silica gel column (2×10 cm) and the solvent was removed under reduced pressure. The resulting oil was crystallized by digesting with petroleum ether/diethyl ether (40/60). The crystals were filtered off and washed with petroleum ether/diethyl ether (40/60). 0.38 g (1.05 mmol, 27.0%) of 6-(diphenylphosphino)-2-pivaloylaminopyridine was obtained as a solid.

後処理

  1. temperatureto warm to ambient temperature overnight
  2. additionby adding 10 ml of dist
  3. customThe resulting phases were separated
  4. extractionthe aqueous phase was extracted twice with 50 ml each time of ethyl acetate
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. filtrationThe residue was filtered together with dichloromethane through a short silica gel column (2×10 cm)
  8. customthe solvent was removed under reduced pressure
  9. customThe resulting oil was crystallized
  10. filtrationThe crystals were filtered off
  11. washwashed with petroleum ether/diethyl ether (40/60)

出典と根拠

ORDレコード
ord-9e9bf29279814d65b7d779cb73d725ca
出典データセット
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07049473B2

反応ノート

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